Bis(4-dimethylaminophenyl)phosphine oxide

Base Information

• Chemical Name: Bis(4-dimethylaminophenyl)phosphine oxide
• CAS No.: 84127-06-0
• Molecular Formula: C₁₆H₂₁N₂OP
• Molecular Weight: 288.329
• DSSTox Substance ID: DTXSID701237431
• ChEMBL ID: CHEMBL1346560
• Mol file: 84127-06-0.mol

Synonyms:MLS001018608;SCHEMBL636857;CHEMBL1346560;RWYIFIGCEJVAED-UHFFFAOYSA-N;DTXSID701237431;HMS2657H05;AKOS001032091;bis(4-dimethylaminophenyl)phosphine oxide;84127-06-0;SMR000354793;bis(4-dimethylaminophenyl)-phosphine oxide;4,4'-Phosphinylidenebis[N,N-dimethylbenzenamine];Z56762374

Chemical Property of Bis(4-dimethylaminophenyl)phosphine oxide

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 287.13132526
• Heavy Atom Count: 20
• Complexity: 286

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN(C)C1=CC=C(C=C1)[P+](=O)C2=CC=C(C=C2)N(C)C

Technology Process of Bis(4-dimethylaminophenyl)phosphine oxide

There total 8 articles about Bis(4-dimethylaminophenyl)phosphine oxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

4-bromo-N,N-dimethylaniline (586-77-6) → bis[4-(N,N-dimethylaminephenyl)]phosphine oxide (84127-06-0)

Guidance literature:

4-bromo-N,N-dimethylaniline; With magnesium; In tetrahydrofuran; at 0 - 20 ℃; for 20.25h; Inert atmosphere;

With phosphonic acid diethyl ester; In tetrahydrofuran; at 0 - 20 ℃; for 20.25h; Inert atmosphere;

DOI:10.1002/adsc.201800723

Reference yield: 71.0%

4-chloro-N,N-dimethylaniline (698-69-1) → bis[4-(N,N-dimethylaminephenyl)]phosphine oxide (84127-06-0)

Guidance literature:

4-chloro-N,N-dimethylaniline; With magnesium; In tetrahydrofuran; at 20 ℃; for 4h; Inert atmosphere; Schlenk technique;

With phosphonic acid diethyl ester; In tetrahydrofuran; at 20 ℃; for 2.25h; Inert atmosphere; Schlenk technique; Cooling with ice;

DOI:10.1021/ja509381w

Reference yield: 57.0%

phosphonic acid diethyl ester (762-04-9) + 4-dimethylaminophenylmagnesium bromide (7353-91-5) → bis[4-(N,N-dimethylaminephenyl)]phosphine oxide (84127-06-0)

Guidance literature:

In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/ol0517832

upstream raw materials:

N,N-dimethyl-aniline

phosphonic acid diethyl ester

4-dimethylaminophenylmagnesium bromide

Diethyl phosphonate

Downstream raw materials:

[Bis-(4-dimethylamino-phenyl)-phosphinoyl]-methanol

bis-(p-dimethylaminophenyl)chloromethylphosphine oxide

bis(4-methoxyphenyl)phosphine

tetrakisbisphosphine

Refernces

• 1、 Krishnamurti, Vinayak,Barrett, Colby,Prakash, G. K. Surya. "Siladifluoromethylation and Deoxo-trifluoromethylation of PV-H Compounds with TMSCF3: Route to PV-CF2- Transfer Reagents and P-CF3 Compounds". supporting information. p. 1526 - 1529. Retrieved 2019/03/07.
• 2、 Provis-Evans, Cei B.,Emanuelsson, Emma A. C.,Webster, Ruth L.. "Rapid Metal-Free Formation of Free Phosphines from Phosphine Oxides". supporting information. p. 3999 - 4004. Retrieved 2018/09/21.